3,5-Bis(trifluoromethyl)benzoyl chloride → N-[4-(2,3-Dimethoxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 878189Notes

Reaction equation

HRID 878189 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[NH:17][CH3:18].[F:19][C:20]([F:35])([F:34])[C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[C:24](Cl)=[O:25]>CCCCCCC.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[N:17]([CH3:18])[C:24](=[O:25])[C:23]1[CH:22]=[C:21]([C:20]([F:35])([F:34])[F:19])[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=1

Participants

4

Reactant 2

HCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 70663228[4-(2,3-Dimethoxy-phenyl)-pyridin-3-yl]-methyl-amine

Product 1

HCID 86670778N-[4-(2,3-Dimethoxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, intermediate, from [4-(2,3-dimethoxy-phenyl)-pyridin-3-yl]-methyl-amine and 3,5-bis(trifluoromethyl)benzoyl chloride (CAS RN 1271-19-8) and using a gradient of n-heptane:EtOAc (100:0 to 40:60) for the chromatographic purification. Light yellow solid (72%). MS (ESI): m/z=485.127 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-c782623779694514830e8cd250111499
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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